Winner of five 2015 Primetime Emmys
Winner of five consecutive Wimbledons
Winner of five gold medals at the '88 Olympics
Winner of five gold medals at the 1980 Winter Olympics
Winner of five golds at Lake Placid
Winner of four 1990s-2000s golf majors
Winner of four 1996 Tony Awards
Winner of four consecutive Olympic gold medals
Winner of four consecutive U.S. Open titles
Winner of four FIFA World Cups
Winner of four gold medals at the Berlin Olympics
Winner of four gold medals in 1936
Winner of four Indy 500s
Winner of four New Age Grammys
Winner of four Outstanding Comedy Series Emmys
Winner of four straight U.S. Opens, 1975-'78
Winner of four World Series in this century, on scoreboards
Winner of more than half of all the World Puzzle Championships
winner of most men s grand slams
winner of most tennis grand slams
Winner of nine golf majors
Winner of nine Grand Slam titles
Winner of nine Grand Slam tournaments in the 1990s
Winner of over 125 Pulitzer Prizes, for short
winner of prize
Winner of seven Emmys
Winner of seven French Opens
Winner of seven straight NCAA hoops championships
Winner of seven tennis majors in the 1920s
Winner of seven Tonys
Winner of seven Tonys in 1977
Winner of seven Tonys in 1980
Winner of seven Wimbledons
Winner of six 2011 Grammys
Winner of six David di Donatello acting awards
Winner of six Grammys in 2012
Winner of six Grand Slam men's singles titles from 1985 to 1992
Winner of six Teen Choice Awards, 1999-2003
Winner of six U.S. Opens
Winner of some Olympic competitions
Winner of Super Bowls VII and VIII
Winner of Superbowl III
Winner of tennis's Grand Slam in 1962 and 1969
Winner of the "Thrilla in Manila"
Winner of the 1942 Masters
Winner of the 1966 World Cup: Abbr
Winner of the 1968 U.S. Open
Winner of the 1970 Hart Trophy, Conn Smythe Trophy, Norris Trophy, and Art Ross Trophy
Winner of the 1976 ABA Slam Dunk contest
Winner of the 1976 Pulitzer Prize for Music
Winner of the 1985 Best New Artist Grammy
Winner of the 1997 and 1998 Super Bowls
Winner of the 1999 Best Foreign Language Film Oscar
Winner of the 2000 Golden Globe for Best Director
Winner of the 2005 and 2007 Grammys for Best Spoken Word Album
Winner of the 2005 Best Picture Oscar
Winner of the 2006 Orange Bowl
Winner of the first FedEx Cup
Winner of the first French Open
Winner of the first slam dunk contest
Winner of the first Super Bowl
Winner of the first three Fiesta Bowls, for short
Winner of the first two Super Bowl MVPs
Winner of the first World Cup: Abbr.
Winner of the first World Series (as the "Americans")
Winner of the four tennis majors and Olympic 8-Down
Winner of the inaugural College Football Playoff
Winner of the lowest-scoring Super Bowl in N.F.L. history (16 total points)
Winner of the most 2016 Olympic medals
Winner of the most French Open singles titles
Winner of the most Grand Slam singles titles in the Open Era
Winner of the most medals at the 2018 Winter Olympics: Abbr.
Winner of the most medals at the 2020 Olympics
Winner of the most singles titles
Winner of the most Women's World Cups
Winner of the Olympics 2010
Winner of the wager in 17-/56-Across, depending on how you fill the circled squares in this puzzle
Winner of three consecutive Emmys for "Mission: Impossible"
Winner of three Grand Slam events
Winner of three Masters
Winner of three of 2000's four majors
Winner of three Oscars in 2013
Winner of three Pulitzer Prizes for Drama
Winner of three Wimbledons
Winner of two Grammys and a Nobel Peace Prize
Winner of two Oscars and two Tonys
Winner of two U.S., three French, and four Australian Opens
Winner of Wimbledon for five consecutive years
winner Oscar
Winner over Alexander in 1804
Winner over NYY in the 2001 World Series
Winner over Ohio State in 1935's so-called "Game of the Century"
Winner over Schmeling in 1938
Winner over the Patriots in Super Bowl XXXI
winner Pageant accessory
winner Preakness
winner Pulitzer 1934 writer
winner Pyle Pulitzer 1934 writer
winner Race
winner Rivera Tony
winner Safin U.S. Open 1955 winner
winner Scott Newbery Medal winner Lowry
winner Styne Tony
winner Surefire
winner Susan Emmy
winner Swoosie Tony
winner Thompson Emmy
winner Tony
winner Triple Crown 1930 jockey
winner U.S. Open 1955 winner
winner Uta Tony
winner Ward Emmy
winner Welty Pulitzer 1934 writer
Winner when heads loses
Winner who finished next to last, in fable
Winner winner chicken dinner!
winner World Cup 1958 sensation
winner Worth Tony
Winner-take-all playground game
Winner, claimed the 11/3/48 Chicago Tribune
Winner, for short
Winner, for sure
Winner, ideally
Winner, informally
Winner, usually
Winner!
Winner's accessory
Winner's attitude
Winner's boast
Winner's check?
Winner's crown
winner's cry
Winner's cry in a card game
Winner's demand
Winner's emotion
Winner's feeling
Winner's flag
Winner's gathering
Winner's gesture
Winner's hand gesture
Winner's haul
Winner's look
Winner's material
Winner's medal metal
Winner's medalla
Winner's number
Winner's overhead gesture
Winner's pair?
Winner's poor sportsmanship
Winner's position
Winner's privilege
Winner's prize
Winner's prize in a programming competition?
Winner's prize on "RuPaul's Drag U"
Winner's prize, in 20-Across
Winner's prize, perhaps
Winner's sign
Winner's signs
Winner's spot
Winner's take
Winner's take, often
Winner's take, perhaps
Winner's take, sometimes
Winner's take?
Winner's token
Winner's two-finger gesture
Winner's victim
Winner's wreath
Winnerless contest
Winnerless game
Winnerless games
Winners
Winners at the Battle of Chickasaw Bayou, for short
Winners break it
winners cry
winners Election data
Winners get them
winners in the ancient olympics received wreaths of crowns made of these leaves
Winners of some televised singing competitions
Winners of Super Bowl 50
Winners of the first World Series, familiarly
Winners of the longest postseason game in major-league history (18 innings, 2005)
winners WWII 1/3 of a film title
winners-cry
Winners' checks?
Winners' counterparts
Winners' flashes
Winners' opposites
Winners' signs
Winners' takes
Winnie ___ (famous plane)
Winnie ___ (Wiley Post's plane)
Winnie ___ Pu
Winnie ___ Pu (Latin version of Milne's classic that became a bestseller in 1960)
Winnie ___ Pu: Latin version of a Milne work
Winnie ____ Pooh
winnie the pooh
Winnie the Pooh and Tigger ___
Winnie the Pooh creator
Winnie the Pooh pal
Winnie the Pooh writer
Winnie-the-___
Winnie-the-___ House
Winnie-the-Pooh baby
Winnie-the-Pooh catchphrase
Winnie-the-Pooh character
Winnie-the-Pooh donkey
Winnie-the-Pooh greeting
Winnie-the-Pooh salutation
Winnie-the-Pooh writer
Winnie-the-Pooh young 'un
Winnie-the-Pooh youngling
Winnie-the-Pooh, e.g.
Winnie-the-Pooh, for one
Winnie-the-Pooh's creator
Winnie-the-Pooh's donkey friend
Winnie-the-Pooh's favorite food
Winnie-the-Pooh's favorite nosh
Winnie-the-Pooh's Hundred ___ Wood
Winnie's husband once
Winnie's title?
Winning
Winning __ everything
Winning ___
Winning ___ everything
Winning ___ everything, it's the only thing (quote attributed to Vince Lombardi)
Winning ___ everything, it's the only thing!
Winning 'Hollywood Squares' line
Winning "Hollywood Squares" line, at times
Winning 1-Across can make this grow
Winning 2004 team, for short
Winning 3-2, e.g.
Winning 4-3, say
Winning a blue ribbon
Winning a race
Winning advantage
Winning again and again
Winning all the games in a series
Winning an Olympic gold medal, for some
Winning an Oscar for "Norma Rae"?
Winning an Oscar, Emmy and Tony, e.g.
Winning an Oscar, Emmy and Tony, for an actor
Winning and then some
Winning and winning
Winning at chess
Winning at craps, say
Winning big
Winning big, real big
Winning Bridge Made Easy author
Winning by a point